CA2575668A1 - Azaindole carboxamides - Google Patents
Azaindole carboxamides Download PDFInfo
- Publication number
- CA2575668A1 CA2575668A1 CA002575668A CA2575668A CA2575668A1 CA 2575668 A1 CA2575668 A1 CA 2575668A1 CA 002575668 A CA002575668 A CA 002575668A CA 2575668 A CA2575668 A CA 2575668A CA 2575668 A1 CA2575668 A1 CA 2575668A1
- Authority
- CA
- Canada
- Prior art keywords
- unsubstituted
- phenyl
- substituted
- alkyl
- piperazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 Azaindole carboxamides Chemical class 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
- 239000000460 chlorine Substances 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
- 229910052801 chlorine Inorganic materials 0.000 claims description 77
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 75
- 239000011737 fluorine Substances 0.000 claims description 73
- 229910052731 fluorine Inorganic materials 0.000 claims description 73
- 229910052794 bromium Inorganic materials 0.000 claims description 67
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 65
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 65
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 238000004519 manufacturing process Methods 0.000 claims description 43
- 239000004202 carbamide Substances 0.000 claims description 40
- 125000001153 fluoro group Chemical group F* 0.000 claims description 38
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 18
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000006193 alkinyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 208000011580 syndromic disease Diseases 0.000 claims description 14
- 210000003169 central nervous system Anatomy 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000018737 Parkinson disease Diseases 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 12
- 150000002390 heteroarenes Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 208000020401 Depressive disease Diseases 0.000 claims description 8
- 206010046543 Urinary incontinence Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 230000006735 deficit Effects 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000031424 hyperprolactinemia Diseases 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 206010003805 Autism Diseases 0.000 claims description 5
- 208000020706 Autistic disease Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 239000003176 neuroleptic agent Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010028813 Nausea Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 239000007825 activation reagent Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- OVJBUNPNGRSPRG-UHFFFAOYSA-N n-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]-5-methyl-4-oxo-7-phenyl-1h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C=1C=CC=CC=1N1C=2NC=NC(=O)C=2C(C)=C1C(=O)NCCCCN(CC1)CCN1C1=CC=CC(Cl)=C1Cl OVJBUNPNGRSPRG-UHFFFAOYSA-N 0.000 claims description 3
- 230000008693 nausea Effects 0.000 claims description 3
- KVAMRUFYUUWMTH-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[4-[4-(2,3,4,5-tetrahydro-1-benzoxepin-9-yl)piperazin-1-yl]butyl]pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1CN(C=2C=3OCCCCC=3C=CC=2)CCN1CCCCNC(=O)C1=CC2=CC=CN=C2N1S(=O)(=O)C1=CC=CC=C1 KVAMRUFYUUWMTH-UHFFFAOYSA-N 0.000 claims description 2
- LGMMIVLQPKONOL-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[4-[4-(2-ethoxyphenyl)piperazin-1-yl]butyl]pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound CCOC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C3=CC=CN=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)CC1 LGMMIVLQPKONOL-UHFFFAOYSA-N 0.000 claims description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
- KYCCFRPSPNTOBO-UHFFFAOYSA-N n-[4-[4-(2,3,4,5-tetrahydro-1-benzoxepin-9-yl)piperazin-1-yl]butyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1CCCOC2=C1C=CC=C2N(CC1)CCN1CCCCNC(=O)C1=CC2=CC=CN=C2N1 KYCCFRPSPNTOBO-UHFFFAOYSA-N 0.000 claims description 2
- KCBQZNVTYOXJHL-UHFFFAOYSA-N n-[4-[4-(2,3,4,5-tetrahydro-1-benzoxepin-9-yl)piperazin-1-yl]butyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1CCCOC2=C1C=CC=C2N(CC1)CCN1CCCCNC(=O)C1=CNC2=NC=CC=C12 KCBQZNVTYOXJHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000026723 Urinary tract disease Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 208000014001 urinary system disease Diseases 0.000 claims 2
- UBBVHQXPFNONTN-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[4-[4-(2,3,4,5-tetrahydro-1-benzoxepin-9-yl)piperazin-1-yl]butyl]pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1CN(C=2C=3OCCCCC=3C=CC=2)CCN1CCCCNC(=O)C(C1=CC=CN=C11)=CN1S(=O)(=O)C1=CC=CC=C1 UBBVHQXPFNONTN-UHFFFAOYSA-N 0.000 claims 1
- ROFYJDSLEZCBOJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[4-[4-(3,4-dihydro-2h-chromen-8-yl)piperazin-1-yl]butyl]pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1CN(C=2C=3OCCCC=3C=CC=2)CCN1CCCCNC(=O)C1=CC2=CC=CN=C2N1S(=O)(=O)C1=CC=CC=C1 ROFYJDSLEZCBOJ-UHFFFAOYSA-N 0.000 claims 1
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 16
- 229960003638 dopamine Drugs 0.000 abstract description 8
- 230000004060 metabolic process Effects 0.000 abstract description 4
- 230000008054 signal transmission Effects 0.000 abstract description 4
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 230000002159 abnormal effect Effects 0.000 abstract 1
- 230000001771 impaired effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000003446 ligand Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 17
- 102000005962 receptors Human genes 0.000 description 17
- 108020003175 receptors Proteins 0.000 description 17
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 13
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- 102000015554 Dopamine receptor Human genes 0.000 description 10
- 108050004812 Dopamine receptor Proteins 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 230000001270 agonistic effect Effects 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- CQMJEZQEVXQEJB-UHFFFAOYSA-N 1-hydroxy-1,3-dioxobenziodoxole Chemical compound C1=CC=C2I(O)(=O)OC(=O)C2=C1 CQMJEZQEVXQEJB-UHFFFAOYSA-N 0.000 description 3
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- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 3
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- 230000003042 antagnostic effect Effects 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Otolaryngology (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004054634A DE102004054634A1 (de) | 2004-11-12 | 2004-11-12 | Azaindolcarboxamide |
| DE102004054634.7 | 2004-11-12 | ||
| PCT/EP2005/012127 WO2006050976A1 (de) | 2004-11-12 | 2005-11-11 | Azaindolcarboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2575668A1 true CA2575668A1 (en) | 2006-05-18 |
Family
ID=35929547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002575668A Abandoned CA2575668A1 (en) | 2004-11-12 | 2005-11-11 | Azaindole carboxamides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20070299091A1 (de) |
| EP (1) | EP1771448A1 (de) |
| JP (1) | JP2008519797A (de) |
| KR (1) | KR20070083843A (de) |
| CN (1) | CN101056878A (de) |
| AU (1) | AU2005303904A1 (de) |
| BR (1) | BRPI0517846A (de) |
| CA (1) | CA2575668A1 (de) |
| DE (1) | DE102004054634A1 (de) |
| EA (1) | EA200700909A1 (de) |
| IL (1) | IL180317A0 (de) |
| MX (1) | MX2007005649A (de) |
| NO (1) | NO20072601L (de) |
| WO (1) | WO2006050976A1 (de) |
| ZA (1) | ZA200700252B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10041479A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung zur Verabreichung von N-0923 |
| EP1547592A1 (de) | 2003-12-23 | 2005-06-29 | Schwarz Pharma Ag | Intranasale formulierung enthaltend |
| DE10361258A1 (de) | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
| DE102004014841B4 (de) | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
| US8748608B2 (en) | 2007-06-15 | 2014-06-10 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | 4-phenylpiperazine derivatives with functionalized linkers as dopamine D3 receptor selective ligands and methods of use |
| US8580803B2 (en) | 2009-12-30 | 2013-11-12 | Arqule, Inc. | Substituted pyrrolo-aminopyrimidine compounds |
| MD20140130A2 (ro) | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| MX2015010714A (es) | 2013-02-19 | 2016-06-14 | Pfizer | Compuestos de azabencimidazol. |
| JP6487921B2 (ja) | 2013-12-17 | 2019-03-20 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規の３，４−二置換−１Ｈ−ピロロ［２，３−ｂ］ピリジンおよび４，５−二置換−７Ｈ−ピロロ［２，３−ｃ］ピリダジン |
| JP6713982B2 (ja) | 2014-07-24 | 2020-06-24 | ファイザー・インク | ピラゾロピリミジン化合物 |
| MX2017001565A (es) | 2014-08-06 | 2017-04-27 | Pfizer | Compuestos de imidazopiridazina. |
| JP2018523665A (ja) | 2015-08-06 | 2018-08-23 | キメリックス インコーポレイテッド | 抗ウイルス剤として有用なピロロピリミジンヌクレオシドおよびその類縁体 |
| WO2017046675A1 (en) | 2015-09-14 | 2017-03-23 | Pfizer Inc. | Novel imidazo [4,5-c] quinoline and imidazo [4,5-c][1,5] naphthyridine derivatives as lrrk2 inhibitors |
| US11299476B2 (en) | 2016-03-14 | 2022-04-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dopamine D3 receptor selective antagonists/partial agonists; method of making; and use thereof |
| WO2018021447A1 (ja) | 2016-07-28 | 2018-02-01 | 塩野義製薬株式会社 | ドーパミンｄ３受容体拮抗作用を有する含窒素縮環化合物 |
| CN106279071B (zh) * | 2016-08-10 | 2019-01-04 | 广东东阳光药业有限公司 | 苯基哌嗪衍生物及其使用方法和用途 |
| US11111264B2 (en) | 2017-09-21 | 2021-09-07 | Chimerix, Inc. | Morphic forms of 4-amino-7-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide and uses thereof |
| EP3744721A4 (de) | 2018-01-26 | 2021-11-10 | Shionogi & Co., Ltd | Kondensierte cyclische verbindung mit dopamin-d3-rezeptor-antagonismus |
| US11447484B2 (en) | 2018-01-26 | 2022-09-20 | Shionogi & Co., Ltd. | Cyclic compound having dopamine D3 receptor antagonistic effect |
| EP3849963A1 (de) | 2018-09-11 | 2021-07-21 | The United States of America, as Represented By the Secretary, Department of Health and Human Services | Dopamin-d3 -rezeptorselektive antagonisten/partielle agonisten und verwendungen davon |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90279A (en) * | 1988-05-24 | 1995-03-30 | American Home Prod | History of piperazinyl carboxamide, their preparation and the pharmaceutical preparations containing them |
| ES2027898A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la 2-metoxifenilpiperacina. |
| WO1994020497A1 (en) * | 1993-03-01 | 1994-09-15 | Merck Sharp & Dohme Limited | Pyrrolo-pyridine derivatives |
| HUP0103987A3 (en) * | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
| CA2489396A1 (en) * | 2002-07-04 | 2004-01-15 | Schwarz Pharma Ag | Utilization of heteroarene carboxamide as dopamine-d3 ligands for the treatment of cns diseases |
| CA2498936C (en) * | 2002-09-14 | 2013-02-12 | Gov't Of The Usa As Represented By The Secretary Of The Department Of Health & Human Services | Structurally rigid dopamine d3 receptor selective ligands and process for making them |
| JP2004123562A (ja) * | 2002-09-30 | 2004-04-22 | Japan Science & Technology Corp | 神経細胞死抑制作用を有する化合物を用いた医薬 |
| AU2004240946B8 (en) * | 2003-05-21 | 2012-01-12 | Prosidion Limited | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase |
| SE0401655D0 (sv) * | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | New compounds |
-
2004
- 2004-11-12 DE DE102004054634A patent/DE102004054634A1/de not_active Ceased
-
2005
- 2005-11-11 CN CNA2005800387992A patent/CN101056878A/zh active Pending
- 2005-11-11 CA CA002575668A patent/CA2575668A1/en not_active Abandoned
- 2005-11-11 EA EA200700909A patent/EA200700909A1/ru unknown
- 2005-11-11 EP EP05805690A patent/EP1771448A1/de not_active Withdrawn
- 2005-11-11 WO PCT/EP2005/012127 patent/WO2006050976A1/de active Application Filing
- 2005-11-11 JP JP2007540597A patent/JP2008519797A/ja active Pending
- 2005-11-11 AU AU2005303904A patent/AU2005303904A1/en not_active Abandoned
- 2005-11-11 KR KR1020077009695A patent/KR20070083843A/ko not_active Application Discontinuation
- 2005-11-11 BR BRPI0517846-0A patent/BRPI0517846A/pt not_active IP Right Cessation
- 2005-11-11 US US11/667,601 patent/US20070299091A1/en not_active Abandoned
- 2005-11-11 MX MX2007005649A patent/MX2007005649A/es not_active Application Discontinuation
-
2006
- 2006-12-25 IL IL180317A patent/IL180317A0/en unknown
-
2007
- 2007-01-09 ZA ZA200700252A patent/ZA200700252B/xx unknown
- 2007-05-22 NO NO20072601A patent/NO20072601L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN101056878A (zh) | 2007-10-17 |
| KR20070083843A (ko) | 2007-08-24 |
| DE102004054634A1 (de) | 2006-05-18 |
| WO2006050976A1 (de) | 2006-05-18 |
| EP1771448A1 (de) | 2007-04-11 |
| EA200700909A1 (ru) | 2007-12-28 |
| MX2007005649A (es) | 2007-07-09 |
| IL180317A0 (en) | 2007-06-03 |
| NO20072601L (no) | 2007-05-22 |
| AU2005303904A1 (en) | 2006-05-18 |
| ZA200700252B (en) | 2009-05-27 |
| BRPI0517846A (pt) | 2008-10-21 |
| JP2008519797A (ja) | 2008-06-12 |
| US20070299091A1 (en) | 2007-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |